Por favor, use este identificador para citar o enlazar a este item:
http://hdl.handle.net/10261/37531
COMPARTIR / EXPORTAR:
SHARE CORE BASE | |
Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL | DATACITE | |
Título: | Synthesis of Thiohydantoin-Castanospermine Glycomimetics as Glycosidase Inhibitors |
Autor: | Aguilar Moncayo, Matilde; Ortiz-Mellet, Carmen; García Fernández, José Manuel CSIC ORCID; García Moreno, María Isabel | Palabras clave: | Animals Biomimetic materials Carbohydrates Enzyme Inhibitors Indolizines Thiohydantoins Glycoside hydrolases |
Fecha de publicación: | 31-mar-2009 | Editor: | American Chemical Society | Citación: | Journal of Organic Chemistry 74(9): 3595-3598 (2009) | Resumen: | The preparation of bicyclic carbohydrate mimics related to (+)-castanospermine incorporating a thiohydantoin moiety is reported. The synthetic approach is compatible with molecular diversity-oriented strategies and involves alpha-azidoesters, built at the C-5/C-6 segment in gluco- or galactofuranose scaffolds, as the key precursors. Reduction to the corresponding alpha-amino ester and in situ coupling with isothiocyanates afford thioureidoester intermediates that undergo spontaneous cyclization to the corresponding hydantoins, beta-elimination, and furanose --> indolizidine rearrangement in a tandem manner. Biological evaluation of the new sp(2)-iminosugar-type glycomimetics evidenced a strong influence of the nature of the substituents at the nitrogen or oxygen atoms on the glycosidase inhibitory properties. | Descripción: | 4 páginas, 2 figuras, 1 tabla, 2 esquemas. | Versión del editor: | http://dx.doi.org/10.1021/jo900231b | URI: | http://hdl.handle.net/10261/37531 | DOI: | 10.1021/jo900231b | ISSN: | 0022-3263 |
Aparece en las colecciones: | (IIQ) Artículos |
Mostrar el registro completo
CORE Recommender
SCOPUSTM
Citations
31
checked on 25-abr-2024
WEB OF SCIENCETM
Citations
24
checked on 26-feb-2024
Page view(s)
371
checked on 27-abr-2024
Google ScholarTM
Check
Altmetric
Altmetric
NOTA: Los ítems de Digital.CSIC están protegidos por copyright, con todos los derechos reservados, a menos que se indique lo contrario.